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Acridine orange information


Acridine orange
Acridine orange
Ball-and-stick model of the acridine orange freebase molecule
Names
Preferred IUPAC name
N,N,N′,N′-Tetramethylacridine-3,6-diamine
Systematic IUPAC name
3-N,3-N,6-N,6-N-Tetramethylacridine-3,6-diamine
Other names
3,6-Acridinediamine

Acridine Orange Base
Acridine Orange NO
Basic Orange 14
Euchrysine
Rhoduline Orange
Rhoduline Orange N
Rhoduline Orange NO
Solvent Orange 15

Waxoline Orange A
Identifiers
CAS Number
  • 494-38-2 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:87346 ☒N
  • hydrochloride: CHEBI:51739
  • cation: CHEBI:52788
ChEMBL
  • ChEMBL81880 checkY
ChemSpider
  • 56136 checkY
ECHA InfoCard 100.122.153 Edit this at Wikidata
EC Number
  • 200-614-0
KEGG
  • C19315 ☒N
MeSH Acridine+orange
PubChem CID
  • 62344
RTECS number
  • AR7601000
UNII
  • F30N4O6XVV checkY
CompTox Dashboard (EPA)
  • DTXSID60197783 Edit this at Wikidata
InChI
  • InChI=1S/C17H19N3/c1-19(2)14-7-5-12-9-13-6-8-15(20(3)4)11-17(13)18-16(12)10-14/h5-11H,1-4H3 checkY
    Key: DPKHZNPWBDQZCN-UHFFFAOYSA-N checkY
  • InChI=1/C17H19N3/c1-19(2)14-7-5-12-9-13-6-8-15(20(3)4)11-17(13)18-16(12)10-14/h5-11H,1-4H3
    Key: DPKHZNPWBDQZCN-UHFFFAOYAJ
SMILES
  • n1c3c(cc2c1cc(N(C)C)cc2)ccc(c3)N(C)C
Properties
Chemical formula
C17H19N3
Molar mass 265.360 g·mol−1
Appearance Orange powder
Hazards
GHS labelling:
Pictograms
GHS06: ToxicGHS07: Exclamation mark
Signal word
Warning
Hazard statements
H302, H312, H341
Precautionary statements
P281, P304+P340
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 0: Will not burn. E.g. waterInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
0
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

Acridine orange is an organic compound that serves as a nucleic acid-selective fluorescent dye with cationic properties useful for cell cycle determination. Acridine orange is cell-permeable, which allows the dye to interact with DNA by intercalation, or RNA via electrostatic attractions. When bound to DNA, acridine orange is very similar spectrally to an organic compound known as fluorescein. Acridine orange and fluorescein have a maximum excitation at 502nm and 525 nm (green). When acridine orange associates with RNA, the fluorescent dye experiences a maximum excitation shift from 525 nm (green) to 460 nm (blue). The shift in maximum excitation also produces a maximum emission of 650 nm (red). Acridine orange is able to withstand low pH environments, allowing the fluorescent dye to penetrate acidic organelles such as lysosomes and phagolysosomes that are membrane-bound organelles essential for acid hydrolysis or for producing products of phagocytosis of apoptotic cells. Acridine orange is used in epifluorescence microscopy and flow cytometry. The ability to penetrate the cell membranes of acidic organelles and cationic properties of acridine orange allows the dye to differentiate between various types of cells (i.e., bacterial cells and white blood cells). The shift in maximum excitation and emission wavelengths provides a foundation to predict the wavelength at which the cells will stain.[1]

  1. ^ Yektaeian, Narjes; Mehrabani, Davood; Sepaskhah, Mozhdeh; Zare, Shahrokh; Jamhiri, Iman; Hatam, Gholamreza (December 2019). "Lipophilic tracer Dil and fluorescence labeling of acridine orange used for Leishmania major tracing in the fibroblast cells". Heliyon. 5 (12): e03073. Bibcode:2019Heliy...503073Y. doi:10.1016/j.heliyon.2019.e03073. PMC 6928280. PMID 31890980.

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Lysosome

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Fluorophore

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cresyl violet, oxazine 170, etc. Acridine derivatives: proflavin, acridine orange, acridine yellow, etc. Arylmethine derivatives: auramine, crystal violet...

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AO

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the atomic symbol for the misidentified chemical element Ausenium. Acridine orange, a fluorescent dye Authorship obfuscation, a privacy technique Ao (surname)...

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Cell cycle analysis

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susceptibility to denaturation at low pH using the metachromatic dye acridine orange, reveals the G1Q, G1A, and G1B cell cycle compartments and also makes...

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and diabetes drugs. Psoralens, coal tars, photo-active dyes (eosin, acridine orange) Musk ambrette, methylcoumarin, lemon oil (may be present in fragrances)...

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Oleocanthal

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apoptosis is tested by treating the lysosomal membrane with acridine orange. Acridine orange radiates a red fluorescent color at an increased concentration...

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Vital stain

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011. PMID 19682624. Hathaway WE, Newby LA, Githens JH (1964). "The Acridine Orange Viability Test Applied to Bone Marrow Cells. I. Correlation with Trypan...

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Conductive polymer

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coworkers first produced electroluminescence in crystalline thin films of acridine orange and quinacrine. In 1960, researchers at Dow Chemical developed AC-driven...

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Helicobacter pylori

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Gram stain, Giemsa stain, H&E stain, Warthin-Starry silver stain, acridine orange stain, and phase-contrast microscopy. It is capable of forming biofilms...

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Chlorophyllin

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benzo[a]pyrene and dibenzo[a,i]pyrene. Chlorophyllin also binds to acridine orange. Chlorophyllin has been validated to exhibit ameliorative effects against...

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NAO

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Observatory New Age Outlaws, a wrestling tag team Sodium oxide (NaO) Nonyl Acridine Orange, a fluorescent die. It can stain cardiolipin content of mitochondria...

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OLED

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They applied high alternating voltages in air to materials such as acridine orange dye, either deposited on or dissolved in cellulose or cellophane thin...

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C17H19N3

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molecular formula C17H19N3 (molar mass : 265.35 g/mol) may refer to: Acridine orange Antazoline Esmirtazapine Mirtazapine This set index page lists chemical...

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GelGreen

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genetics for agarose gel DNA electrophoresis. GelGreen consists of two acridine orange subunits that are bridged by a linear oxygenated spacer. Its fluorophore...

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Liposome

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of phosphatidylcholine liposomes, which were stained with fluorochrome acridine orange. Method of fluorescence microscopy (1250-fold magnification)....

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Diagnosis of malaria

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parasites. The blood is taken in a QBC capillary tube which is coated with acridine orange (a fluorescent dye) and centrifuged; the fluorescing parasites can...

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IARC group 3

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list is uptodate as of January 2024. Acenaphthene Acepyrene Aciclovir Acridine orange Acriflavinium chloride Acrylic acid Acrylic fibres Acrylonitrile-butadiene-styrene...

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33239-19-9 Acridine orange Euchrysine Basic Orange 14 46005 acridine 494-38-2 Acridine red 3B 45000 pyronin 2465-29-4 Acriflavine Trypaflavine 46000 acridine 65589-70-0...

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Sonodynamic therapy

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previously in PDT) include acridine orange, methylene blue, curcumin, and indocyanine green. A study by Suzuki et al. used acridine orange, a fluorescent cationic...

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Escherichia coli in molecular biology

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Joshua Lederberg and colleagues) and then in 1985 of the F plasmid by acridine orange curing.[citation needed] Strains derived from MG1655 include DH1, parent...

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Bacterioplankton counting methods

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that is identified through the lens. Fluorescent dyes include DAPI, Acridine Orange, SYBR Green 1, and YO-PRO-1, all of which are capable of staining both...

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Sperm Chromatin Structure Assay

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treatment opens up defective sperm DNA at the sites of damage. Through acridine orange (AO) staining, AO molecules are intercalated into double-stranded DNA...

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